The role of the Chief Information Officer (CIO) is one of facilitating executive decisions regarding the innovation, provision and use of state-of-the-art Information and Communication Technologies (ICT). The aim of this paper is to investigate CIO perceptions of strategy and ICT investment through qualitative interviews with CIOs from leading UK financial sector organisations. We were keen to find out how these executives strategise while coping with the increasing ubiquity and complexity of ICT on one hand and hyper business pressures on the other. As the title suggests, we found that recent changes in the market conditions, as well as in the trust bestowed technology as an agent for radical change, have had serious consequences for the perceptions of risk, strategy and ICT investment. CIOs expressed the dot-com boom to bust transition in terms of a shift from a higher-risk, top-down technology led strategy centred on killer applications towards a lower-risk, bottom-up, organic approach to strategy with the purpose of providing open, user driven enabling infrastructures for competitive advantage. We also note the implications of these trends for the value assessment activity and the enhanced value skill base which information age professionals would increasingly need.